Benzyl Chloride → 4-Benzyloxy-1-butanol

HRID 487470Notes

Reaction equation

HRID 487470 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[CH2:4][CH2:5][CH2:6][OH:7].[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C)C=O>[CH2:9]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][OH:8])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 80641,4-ButanediolHCID 24758Sodium hydride

Product 1

HCID 5622124-Benzyloxy-1-butanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6 g (0.2 mol) of a sodium hydride dispersion (80% in white oil) are placed at room temperature in 120 ml of absolute dimethylformamide, and 22.2 ml (0.25 mol) of 1,4-butanediol are added dropwise. When the addition is complete, the mixture is stirred for a further 30 minutes at room temperature. 23.1 ml (0.2 mol) of benzyl chloride are then slowly added dropwise, a slight exothermic reaction being observed. The reaction mixture is stirred overnight at room temperature, water/ice is added, and the mixture is extracted twice with ether. The organic phases are washed with water and with saturated sodium chloride solution, combined, dried over MgSO4, filtered and concentrated by evaporation. The residue is subjected to fractional distillation under a water-jet vacuum over a 10 cm Vigreux column. 4-benzyloxybutanol is obtained, b.p.22 =161°-162°.

Workup

  1. additionWhen the addition
  2. customa slight exothermic reaction
  3. stirringThe reaction mixture is stirred overnight at room temperature
  4. extractionthe mixture is extracted twice with ether
  5. washThe organic phases are washed with water and with saturated sodium chloride solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. distillationThe residue is subjected to fractional distillation under a water-jet vacuum over a 10 cm Vigreux column

Sources & evidence

ORD record
ord-e6258e9d9bc64d70a27b38b308ddb05a
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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